Apartments in Province of Siena and Villas – Holiday Lettings - Holiday Rentals Province of Siena

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6,195 Holiday homes

(15) Excellent 

Certificate of Excellence

10

Holiday townhouse with swimming pool in Sovicille

Province of Siena / Sovicille

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Nearest beach 72 km
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £98 / night

£686 / week

Book View

Responds fast!
avg. 3 hours 57 minutes

from £98 / night

(19) Very Good 

Certificate of Excellence

19

San Gimignano holiday villa accommodation

Province of Siena / San Gimignano

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 30 km
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £79 / night

£550 - £950 / week

Book View

Responds fast!
avg. 2 hours 22 minutes

from £79 / night

12

Apartment rental in Radicondoli with shared pool

Province of Siena / Radicondoli

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £72 / night

£490 - £686 / week

Book View

from £72 / night

(3) Excellent 

22

Villa rental in Radicondoli with swimming pool

Province of Siena / Radicondoli

5 10 3 nights min

  • 5 bedrooms
  • sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £401 / night

£2,759 / week

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from £401 / night

(2) Excellent 

20

Holiday farmhouse in San Gimignano

Province of Siena / San Gimignano

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 45 km
  • Swimming pool
  • Child friendly

from £71 / night

£488 - £1,021 / week

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from £71 / night

7

Sarteano holiday farmhouse rental

Province of Siena / Sarteano

4 9 3 nights min

  • 4 bedrooms
  • sleeps 9
  • 3 nights min
  • Child friendly

from £374 / night

£2,617 / week

Book View

from £374 / night

(1) Excellent 

12

Holiday home rental

Province of Siena / Montepulciano

4 8 1 night min

  • 4 bedrooms
  • sleeps 8
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

from £312 / night

£2,181 / week

Book View

from £312 / night

(31) Excellent 

Certificate of Excellence

127

Cottage rental in Pancole

San Gimignano / Pancole

1 3 2 nights min

  • 1 bedroom
  • sleeps 3
  • 2 nights min
  • Nearest beach 90 km
  • Child friendly
  • Air conditioning

Certificate of Excellence

from £45 / night

£299 - £330 / week

Book View

Responds fast!
avg. 34 minutes

from £45 / night

17

Holiday home in Radicondoli

Province of Siena / Radicondoli

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child friendly
  • Pet friendly

from £178 / night

£1,246 - £1,469 / week

Book View

from £178 / night

(4) Excellent 

16

Farmhouse rental in Radicofani with shared pool

Province of Siena / Radicofani

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £107 / night

£533 - £754 / week

Book View

Responds fast!
avg. 3 hours 44 minutes

from £107 / night

(6) Excellent 

26

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £95 / night

£666 - £972 / week

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from £95 / night

20

Holiday villa rental

Sovicille / Torri

1 4 4 nights min

  • 1 bedroom
  • sleeps 4
  • 4 nights min
  • Child friendly
  • Air conditioning
  • Ask about pets

from £80 / night

£445 / week

Book View

from £80 / night

(2) Excellent 

18

Apartment rental in Radda in Chianti with shared pool

Province of Siena / Radda in Chianti

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Nearest beach 140 km
  • Swimming pool
  • Child friendly

from £80 / night

£561 / week

Book View

from £80 / night

(1) Very Good 

17

Townhouse rental in Sovicille

Province of Siena / Sovicille

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child friendly
  • Ask about pets
  • Private garden

from £54 / night

£339 / week

Book View

Responds fast!
avg. 2 hours 42 minutes

from £54 / night

43

Villa letting in Sarteano with swimming pool

Province of Siena / Sarteano

10 17 1 night min

  • 10 bedrooms
  • sleeps 17
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £356 / night

£2,492 / week

Book View

Responds fast!
avg. 56 minutes

from £356 / night

(2) Excellent 

21

Holiday guest house in Radicondoli

Province of Siena / Radicondoli

3 5 4 nights min

  • 3 bedrooms
  • sleeps 5
  • 4 nights min
  • Nearest beach 60 km
  • Suitable for children age 5+
  • Ask about pets

from £143 / night

£712 / week

Book View

from £143 / night

(16) Excellent 

17

Siena holiday home rental

Province of Siena / Siena

2 3 3 nights min

  • 2 bedrooms
  • sleeps 3
  • 3 nights min
  • Nearest beach 95 km
  • Child friendly
  • Pet friendly

from £76 / night

£530 / week

Book View

from £76 / night

(1) Excellent 

24

Sarteano holiday townhouse rental

Province of Siena / Sarteano

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Suitable for children age 5+

from £72 / night

£499 / week

Book View

from £72 / night

(10) Excellent 

32

Holiday home with swimming pool in Radicondoli

Province of Siena / Radicondoli

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly

from £102 / night

£712 - £1,202 / week

Book View

from £102 / night

11

Holiday farmhouse rental

Province of Siena / Montepulciano

9 18 4 nights min

  • 9 bedrooms
  • sleeps 18
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Private garden

from £712 / night

£3,649 / week

Book View

Responds fast!
avg. 2 hours 7 minutes

from £712 / night

43

San Gimignano holiday b&b accommodation

Province of Siena / San Gimignano

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

from £49 / night

£343 / week

Book View

from £49 / night

(18) Very Good 

Certificate of Excellence

18

Apartment rental in Siena

Province of Siena / Siena

1 4 5 nights min

  • 1 bedroom
  • sleeps 4
  • 5 nights min
  • Nearest beach 105 km
  • Swimming pool
  • Car not necessary

Certificate of Excellence

from £88 / night

£986 / week

Book View

Responds fast!
avg. 2 hours 49 minutes

from £88 / night

20

B&b rental in Chiusure with shared pool

Buonconvento / Chiusure

6 14 3 nights min

  • 6 bedrooms
  • sleeps 14
  • 3 nights min
  • Nearest beach 87 km
  • Swimming pool
  • Child friendly

from £98 / night

£757 / week

Book View

from £98 / night

(13) Excellent 

19

Holiday apartment in Montepulciano

Province of Siena / Montepulciano

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child friendly

from £100 / night

£601 - £875 / week

Book View

from £100 / night

22

Holiday villa with swimming pool in Montisi

Province of Siena / Montisi

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Nearest beach 30 km
  • Swimming pool
  • Child friendly

from £143 / night

£998 - £2,032 / week

Book View

Responds fast!
avg. 1 hour 45 minutes

from £143 / night

(1) Excellent 

21

Holiday farmhouse with swimming pool in Sarteano

Province of Siena / Sarteano

6 12 7 nights min

  • 6 bedrooms
  • sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £229 / night

£1,602 / week

Book View

from £229 / night

(11) Very Good 

47

Holiday farmhouse in Castelnuovo Berardenga

Province of Siena / Castelnuovo Berardenga

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child friendly
  • Ask about pets

from £80 / night

£555 / week

Book View

from £80 / night

12

Radicofani holiday apartment rental

Province of Siena / Radicofani

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £76 / night

£528 / week

Book View

Responds fast!
avg. 3 hours 37 minutes

from £76 / night

6

Holiday apartment letting

Casole d'Elsa / Monteguidi

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

from £102 / night

£604 - £1,139 / week

Book View

Responds fast!
avg. 3 hours 12 minutes

from £102 / night

14

Ski apartment to rent in Pienza

Province of Siena / Pienza

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Ski
  • Child friendly
  • Pet friendly

from £63 / night

£356 / week

Book View

from £63 / night

(1) Excellent 

18

Farmhouse rental in Montepulciano with shared pool

Province of Siena / Montepulciano

7 4 3 nights min

  • 7 bedrooms
  • sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £103 / night

£717 / week

Book View

from £103 / night

(4) Excellent 

22

Holiday apartment with shared pool in Le Piazze

Province of Siena / Le Piazze

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £63 / night

£445 - £712 / week

Book View

from £63 / night

(8) Very Good 

20

Holiday apartment in Monticiano

Province of Siena / Monticiano

2 7 2 nights min

  • 2 bedrooms
  • sleeps 7
  • 2 nights min
  • Child friendly
  • Ask about pets
  • Private garden

from £71 / night

£497 / week

Book View

from £71 / night

(3) Very Good 

20

Pienza holiday home rental

Province of Siena / Pienza

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child friendly
  • Private garden

from £89 / night

£533 - £905 / week

Book View

from £89 / night

44

Holiday villa with swimming pool in Castellina In Chianti

Province of Siena / Castellina In Chianti

6 13 1 night min

  • 6 bedrooms
  • sleeps 13
  • 1 night min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly

from £496 / night

£3,471 - £5,607 / week

Book View

from £496 / night

(1) Excellent 

36

Holiday home in Rigomagno

Sinalunga / Rigomagno

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £83 / night

£579 - £1,326 / week

Book View

from £83 / night

9

Holiday home letting

Province of Siena / Sarteano

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £178 / night

£1,068 / week

Book View

Responds fast!
avg. 2 hours 7 minutes

from £178 / night

4

Holiday hotel apartment with shared pool in Celle sul Rigo

San Casciano dei Bagni / Celle sul Rigo

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool

from £64 / night

£445 / week

Book View

from £64 / night

(1) Excellent 

18

Holiday apartment rental

Province of Siena / Montepulciano

2 7 min stay varies

  • 2 bedrooms
  • sleeps 7
  • min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

from £55 / night

£365 - £877 / week

Book View

Responds fast!
avg. 1 hour 30 minutes

from £55 / night

(1) Excellent 

18

Holiday villa with shared pool in Val d'Orcia

Montalcino / Val d'Orcia

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 25 km
  • Swimming pool
  • Child friendly

from £89 / night

£573 - £1,194 / week

Book View

Responds fast!
avg. 1 hour 45 minutes

from £89 / night

Top Destination reviews

Farmhouse in old mill in the Chianti hills
A fantastic Tuscany retreat

We spent 2 weeks in the guest residence and found the location ideal to visit all of the wonders Tuscany has to offer with even a train station that will take you to Siena in 15 minutes within walking distance if you prefer not to drive. Monteriggioni is a short walk away along footpaths and the whole area is beautiful. The property had everything we as a family of 4 needed plus the added Tuscany charm of a traditional building. My children used the pool every day we were there and we couldn't fault the pool area and gardens for appearance and facilities. The owners are very friendly, available when you need them and can offer a lot of help with deciding where to go or on practical matters such as which supermarket to go to. We were also helped out by the owners with a wine tour booking while we were there which we enjoyed thoroughly. We left with a lot of fond memories of our stay and a camera full of beautiful photographs.see more
Casa Felice is a 2 bedroom apartment in village of Gaiole, sleeps 6, shared pool
Great Location in heart of Tuscany

We had a lovely stay in Case Felice. Well equipped apartment with fantastic views. The Borgo complex was perfect, we enjoyed a swim most days. The village is about 5 mins walk away with plenty of restaurants and a local co-op. We visited Florence (park on outskirts and got the tram in), Siena (our favourite), Pisa, Monteriggioni, San Gimignano (gets very busy, go early or later in afternoon), Radda and Panzano (recommend MacDarios for an excellent burger!)see more
SIENA,villa,pool,tennis,relax,near Piazza IL CAMPO
Ms

A wonderful villa set on top of a hill with very kind and attentive hosts. They have an eye for detail and a strong goal to deliver a clean fully functioning villa so that you can relax and it works! We spent two weeks here and just got so relaxed that after the first week and the excitement of the Palio, we stopped going to Siena every day and started hanging out at the beautiful pool area. Lazy I know but with such a beautiful view it is hard to resist. Andrea, his wife Elizabetta, and their son Thiago do a great job together. Each has their role. They leave you alone if you are comfortable on your own but if you want something they are there to help in an instant. Their house is the main villa on the property and their front door approachable so you can find them when you need or just say ciao and walk to the pool. It is up to you and they make you feel like you can choose either option depending on your day. They do a really good job as hosts. As for the villa the photos are accurate. I have gone back and checked and what you see in those shots is exactly how it looks. Note the clean modern kitchen and bathrooms. You might not appreciate quite how large the upstairs bedrooms are. They are huge airy and very comfortable with aircon. The downstairs bedroom is best for a child. A flyscreen on the bigger window in this room would help in the hottest part of summer. We would return here and wish the family all the best. Heathersee more
Le Fontanelle - rustic farm buildings with pool
Fab stay in Tuscan hills

We enjoyed a lovely relaxing family holiday at this spacious property in the Tuscan hills. Lots to see and do in the area with plenty of lovely food and good local wines. San Gim is close-by with Florence, Volterra, Pisa, and the Chianti region all easily accessible. … see more
Castello di Montalto - 3 Bedroom Villa in Chianti
Beautiful hideaway

We stayed here for 2 weeks and had an amazing time. Beautiful castle in idyllic setting with really authentic feel. Lovely people in charge who made us feel welcome. Only very minor comments would be that some of the equipment needs an upgrade - bikes weren’t really fit for purpose, lights in bbq area didn’t work, bbq equipment not great Overall a place I would return to.see more
Elegant 2 bedroom apt. in historic Siena residence
Beautiful historic apartment!

The apartment is beautiful, in a historic tower that was built prior to 1070. The views from the apartment are stunning. Great location in city center, on a pedestrian street. Andrea was wonderful to communicate with and met us upon arrival. When in Siena, we recommend this apartment. … see more

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